Ultimate MCQ Quiz: Haloalkanes & Haloarenes 🧪

Topic 1: Classification & Nomenclature

  1. 1. The compound C₆H₅CH₂Cl is an example of a:

    a) Aryl halide

    b) Vinylic halide

    c) Benzylic halide

    d) Allylic halide

    Show Answer

    c) Benzylic halide

  2. 2. IUPAC name of CH₃CH(Br)CH₂CH(CH₃)₂ is:

    a) 2-Bromo-4-methylpentane

    b) 4-Bromo-2-methylpentane

    c) 2-Methyl-4-bromopentane

    d) 3-Bromo-1,1-dimethylbutane

    Show Answer

    b) 4-Bromo-2-methylpentane

  3. 3. Which of the following is a gem-dihalide?

    a) 1,2-Dichloropropane

    b) 1,3-Dichloropropane

    c) 2,2-Dichloropropane

    d) 1,4-Dichlorobutane

    Show Answer

    c) 2,2-Dichloropropane

  4. 4. A tertiary alkyl halide is:

    a) 1-Chlorobutane

    b) 2-Chlorobutane

    c) 2-Chloro-2-methylpropane

    d) 1-Chloro-2-methylpropane

    Show Answer

    c) 2-Chloro-2-methylpropane

  5. 5. How many chiral carbons are present in 2-Bromo-3-methylpentane?

    a) 0

    b) 1

    c) 2

    d) 3

    Show Answer

    c) 2 (at C-2 and C-3)

Topic 2: Methods of Preparation

  1. 6. Best reagent for converting an alcohol to an alkyl chloride is:

    a) PCl₅

    b) PCl₃

    c) SOCl₂

    d) HCl + ZnCl₂

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    c) SOCl₂ (Darzen's process)

  2. 7. The addition of HBr to propene in the absence of peroxides gives:

    a) 1-Bromopropane

    b) 2-Bromopropane

    c) 1,2-Dibromopropane

    d) Allyl bromide

    Show Answer

    b) 2-Bromopropane (Markovnikov's rule)

  3. 8. Finkelstein reaction is an example of a:

    a) Halide exchange reaction

    b) Free radical substitution

    c) Electrophilic addition

    d) Nucleophilic substitution

    Show Answer

    a) Halide exchange reaction

  4. 9. Sandmeyer's reaction uses which catalyst?

    a) Anhydrous AlCl₃

    b) Copper powder

    c) Cuprous halide (CuX)

    d) Iron filings

    Show Answer

    c) Cuprous halide (CuX)

  5. 10. The reaction of toluene with Cl₂ in the presence of sunlight gives:

    a) o-Chlorotoluene

    b) p-Chlorotoluene

    c) Benzyl chloride

    d) A mix of o- and p-chlorotoluene

    Show Answer

    c) Benzyl chloride (Free radical substitution on side chain)

Topic 3: Physical Properties & Nature of C-X Bond

  1. 11. Which compound has the highest boiling point?

    a) n-Butyl chloride

    b) sec-Butyl chloride

    c) isobutyl chloride

    d) tert-Butyl chloride

    Show Answer

    a) n-Butyl chloride (Least branching, largest surface area)

  2. 12. The correct order of boiling points for alkyl halides is:

    a) R-F > R-Cl > R-Br > R-I

    b) R-I > R-Br > R-Cl > R-F

    c) R-Cl > R-Br > R-I > R-F

    d) R-F > R-I > R-Br > R-Cl

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    b) R-I > R-Br > R-Cl > R-F (Boiling point increases with atomic mass of halogen)

  3. 13. Which of the following has the highest dipole moment?

    a) CH₃F

    b) CH₃Cl

    c) CH₃Br

    d) CH₃I

    Show Answer

    b) CH₃Cl (Due to the combined effect of electronegativity and bond length)

  4. 14. The correct order of C-X bond length is:

    a) C-F < C-Cl < C-Br < C-I

    b) C-I < C-Br < C-Cl < C-F

    c) C-Cl < C-F < C-Br < C-I

    d) C-F < C-I < C-Br < C-Cl

    Show Answer

    a) C-F < C-Cl < C-Br < C-I (Increases with the size of the halogen atom)

Topic 4: Nucleophilic Substitution (Sₙ1 & Sₙ2) & Stereochemistry

  1. 15. The Sₙ1 reaction mechanism involves the formation of a:

    a) Transition state

    b) Carbocation intermediate

    c) Carbanion intermediate

    d) Free radical

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    b) Carbocation intermediate

  2. 16. Which of the following is most reactive towards Sₙ2 reaction?

    a) (CH₃)₃C-Cl

    b) (CH₃)₂CH-Cl

    c) CH₃CH₂-Cl

    d) CH₃-Cl

    Show Answer

    d) CH₃-Cl (Least steric hindrance)

  3. 17. An Sₙ2 reaction at an asymmetric carbon of a compound always gives:

    a) A product with the same optical rotation

    b) A single stereoisomer

    c) A product with opposite optical rotation (inversion)

    d) A racemic mixture

    Show Answer

    c) A product with opposite optical rotation (inversion)

  4. 18. The order of reactivity of alkyl halides in Sₙ1 reaction is:

    a) 1° > 2° > 3°

    b) 3° > 2° > 1°

    c) 2° > 3° > 1°

    d) 1° > 3° > 2°

    Show Answer

    b) 3° > 2° > 1° (Based on stability of carbocation)

  5. 19. Racemization occurs in which type of reaction?

    a) Sₙ1 reaction

    b) Sₙ2 reaction

    c) E1 reaction

    d) E2 reaction

    Show Answer

    a) Sₙ1 reaction (Due to planar carbocation intermediate)

  6. 20. Which of the following has the best leaving group?

    a) F⁻

    b) Cl⁻

    c) Br⁻

    d) I⁻

    Show Answer

    d) I⁻ (It is the weakest base)

  7. 21. Reaction of ethyl chloride with KCN gives:

    a) Ethyl isocyanide

    b) Propane nitrile

    c) Ethane nitrile

    d) Propylamine

    Show Answer

    b) Propane nitrile (KCN is ionic, C-C bond forms)

  8. 22. Reaction of ethyl chloride with AgCN gives:

    a) Ethyl isocyanide

    b) Propane nitrile

    c) Ethane nitrile

    d) Propylamine

    Show Answer

    a) Ethyl isocyanide (AgCN is covalent, attack occurs through N)

Topic 5: Elimination & Other Reactions

  1. 23. Dehydrohalogenation of an alkyl halide is carried out using:

    a) Aqueous KOH

    b) Alcoholic KOH

    c) Dilute HCl

    d) Water

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    b) Alcoholic KOH

  2. 24. The major product of the dehydrohalogenation of 2-Bromopentane is:

    a) Pent-1-ene

    b) Pent-2-ene

    c) Pent-1-yne

    d) cis-Pent-2-ene

    Show Answer

    b) Pent-2-ene (Saytzeff's Rule - more substituted alkene is major)

  3. 25. Grignard reagent is prepared by reacting an alkyl halide with:

    a) Sodium in dry ether

    b) Magnesium in dry ether

    c) Zinc in alcohol

    d) Copper powder

    Show Answer

    b) Magnesium in dry ether

  4. 26. Wurtz reaction of methyl bromide with sodium in dry ether gives:

    a) Methane

    b) Ethane

    c) Propane

    d) Ethene

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    b) Ethane

Topic 6: Reactions of Haloarenes

  1. 27. Haloarenes are less reactive than haloalkanes towards nucleophilic substitution because of:

    a) Resonance effect

    b) Difference in hybridization of C-atom in C-X bond

    c) Instability of phenyl cation

    d) All of the above

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    d) All of the above

  2. 28. The reaction of Chlorobenzene with Sodium in dry ether gives Biphenyl. This reaction is called:

    a) Wurtz reaction

    b) Wurtz-Fittig reaction

    c) Fittig reaction

    d) Sandmeyer reaction

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    c) Fittig reaction

  3. 29. In electrophilic substitution of chlorobenzene, the chlorine atom acts as:

    a) An activating and o,p-directing group

    b) A deactivating and m-directing group

    c) A deactivating and o,p-directing group

    d) An activating and m-directing group

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    c) A deactivating and o,p-directing group

  4. 30. The presence of a -NO₂ group at the ortho position of chlorobenzene ________ the reactivity towards nucleophilic substitution.

    a) increases

    b) decreases

    c) does not change

    d) first increases then decreases

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    a) increases (due to its electron-withdrawing nature)

  5. 31. Wurtz-Fittig reaction involves:

    a) Two molecules of aryl halide

    b) Two molecules of alkyl halide

    c) One molecule of aryl halide and one molecule of alkyl halide

    d) One molecule of aryl halide and one molecule of alcohol

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    c) One molecule of aryl halide and one molecule of alkyl halide

  6. 32. Which of the following is most reactive to electrophilic substitution?

    a) Chlorobenzene

    b) Benzene

    c) Nitrobenzene

    d) Benzoic acid

    Show Answer

    b) Benzene (Halogens are deactivating)

  7. 33. Dow's process converts chlorobenzene to phenol using:

    a) Steam at high temperature

    b) Aqueous NaOH at 623K and 300 atm

    c) Dilute H₂SO₄

    d) Water in the presence of sunlight

    Show Answer

    b) Aqueous NaOH at 623K and 300 atm